N,N-Diformylmescaline: A novel analogue of mescaline detected in Queensland.

N,N-Diformylmescaline, a novel analogue of mescaline, has recently been detected in Australia in two unrelated seizures. To confirm the identification, a three-step synthesis from 3,4,5-trimethoxyphenylacetic acid was devised. However, purification of the final product proved problematic with the compound prone to degradation in solution.

Unusual 4-arsonoanilinium cationic species in the hydrochloride salt of (4-aminophenyl)arsonic acid and formed in the reaction of the acid with copper(II) sulfate, copper(II) chloride and cadmium chloride.

Structures having the unusual protonated 4-arsonoanilinium species, namely in the hydrochloride salt, CHAsNO·Cl, (I), and the complex salts formed from the reaction of (4-aminophenyl)arsonic acid (p-arsanilic acid) with copper(II) sulfate, i.e. hexaaquacopper(II) bis(4-arsonoanilinium) disulfate dihydrate, (CHAsNO)[Cu(HO)](SO)·2HO, (II), with copper(II) chloride, i.

Crystal structures and hydrogen bonding in the isotypic series of hydrated alkali metal (K, Rb and Cs) complexes with 4-amino-phenyl-arsonic acid.

The structures of the alkali metal (K, Rb and Cs) complex salts with 4-amino-phenyl-arsonic acid (-arsanilic acid) manifest an isotypic series with the general formula [(CHAsNO)(HO)], with = K {poly[di-μ-4-amino-phenyl-arsonato-tri-μ-aqua-dipotassium], [K(CHAsNO)(HO)], (I)}, Rb {poly[di-μ-4-amino-phenyl-arsonato-tri-μ-aqua-dirubidium], [Rb(CHAsNO)(HO)], (II)}, and Cs {poly[di-μ-4-amino-phenyl-arsonato-tri-μ-aqua-dirubidium], [Cs(CHAsNO)(HO)], (III)}, in which the repeating structural units lie across crystallographic mirror planes containing two independent and different metal cations and a bridging water mol-ecule, with the two hydrogen -arsanilate ligands and the second water mol-ecule lying outside the mirror plane. The bonding about the two metal cations in all complexes is similar, one five-coordinate, the other progressing from five-coordinate in (I) to eight-coordinate in both (II) and (III), with overall -O bond-length ranges of 2.694 (5)-3.

The coordination complex structures and hydrogen bonding in the three-dimensional alkaline earth metal salts (Mg, Ca, Sr and Ba) of (4-aminophenyl)arsonic acid.

(4-Aminophenyl)arsonic acid (p-arsanilic acid) is used as an antihelminth in veterinary applications and was earlier used in the monosodium salt dihydrate form as the antisyphilitic drug atoxyl. Examples of complexes with this acid are rare. The structures of the alkaline earth metal (Mg, Ca, Sr and Ba) complexes with (4-aminophenyl)arsonic acid (p-arsanilic acid) have been determined, viz.

Crystal structure and hydrogen bonding in the water-stabilized proton-transfer salt brucinium 4-amino-phenyl-arsonate tetra-hydrate.

In the structure of the brucinium salt of 4-amino-phenyl-arsonic acid (p-arsanilic acid), systematically 2,3-dimeth-oxy-10-oxostrychnidinium 4-amino-phenyl-ar-son-ate tetra-hydrate, (C23H27N2O4)[As(C6H7N)O2(OH)]·4H2O, the brucinium cations form the characteristic undulating and overlapping head-to-tail layered brucine substructures packed along [010]. The arsanilate anions and the water mol-ecules of solvation are accommodated between the layers and are linked to them through a primary cation N-H⋯O(anion) hydrogen bond, as well as through water O-H⋯O hydrogen bonds to brucinium and arsanilate ions as well as bridging water O-atom acceptors, giving an overall three-dimensional network structure.

Crystal structures and hydrogen bonding in the proton-transfer salts of nicotine with 3,5-di-nitro-salicylic acid and 5-sulfosalicylic acid.

The structures of the 1:1 anhydrous salts of nicotine (NIC) with 3,5-di-nitro-salicylic acid (DNSA) and 5-sulfosalicylic acid (5-SSA), namely (1R,2S)-1-methyl-2-(pyridin-3-yl)-1H-pyrrolidin-1-ium 2-carb-oxy-4,6-di-nitro-phenolate, C10H15N2 (+)·C7H3N2O7 (-), (I), and (1R,2S)-1-methyl-2-(pyridin-3-yl)-1H-pyrrolidin-1-ium 3-carb-oxy-4-hy-droxy-benzene-sulfonate, C10H15N2 (+)·C7H5O6S(-), (II), are reported. The asymmetric units of both (I) and (II) comprise two independent nicotinium cations (C and D) and either two DNSA or two 5-SSA anions (A and B), respectively. One of the DNSA anions shows a 25% rotational disorder in the benzene ring system.

The three-dimensional hydrogen-bonded structures in the ammonium and sodium salt hydrates of 4-aminophenylarsonic acid.

The structures of two hydrated salts of 4-aminophenylarsonic acid (p-arsanilic acid), namely ammonium 4-aminophenylarsonate monohydrate, NH4(+)·C6H7AsNO3(-)·H2O, (I), and the one-dimensional coordination polymer catena-poly[[(4-aminophenylarsonato-κO)diaquasodium]-μ-aqua], [Na(C6H7AsNO3)(H2O)3]n, (II), have been determined. In the structure of the ammonium salt, (I), the ammonium cations, arsonate anions and water molecules interact through inter-species N-H..

4-(4-Amino-phenyl-sulfon-yl)anilinium toluene-4-sulfonate.

In the title p-toluene-sulfonate salt of the drug dapsone, C12H13N2O2S(+)·C7H7O3S(-), the dihedral angle between the two aromatic rings of the dapsone monocation is 70.19 (17)° and those between these rings and that of the p-toluene-sulfonate anion are 72.34 (17) and 46.

Investigation of the l-phenylacetylcarbinol process to substituted benzaldehydes of interest.

The large scale industrial manufacture of the nasal decongestant pseudoephedrine is typically carried out by the reductive amination of l-phenylacetylcarbinol (l-PAC), which in turn is produced via the biotransformation of benzaldehyde using yeast. In recent years there has been increasing legislative control of the supply of pseudoephedrine due to it being diverted for the clandestine production of methylamphetamine and there is some evidence that a number of clandestine drug laboratory chemists have considered the application of the l-PAC process to manufacture their own pseudoephedrine. This work examined the use of a number of substituted benzaldehydes for the manufacture of the corresponding substituted l-PAC analogue followed by reductive amination to the corresponding substituted pseudoephedrine/ephedrine analogues.

4-Meth-oxy-anilinium 2-carb-oxy-4,5-di-chloro-benzoate.

In the title salt C7H10NO(+)·C8H3Cl2O4 (-) the benzene rings of the cation and anion are essentially parallel [inter-ring dihedral angle 4.8 (2)°]. In the anion the carb-oxy-lic acid and carboxyl-ate groups make dihedral angles of 19.

Three-dimensional hydrogen-bonded structures in the hydrated proton-transfer salts of isonipecotamide with the dicarboxylic oxalic and adipic acid homologues.

The structures of the 1:1 hydrated proton-transfer compounds of isonipecotamide (piperidine-4-carboxamide) with oxalic acid, 4-carbamoylpiperidinium hydrogen oxalate dihydrate, C6H13N2O(+)·C2HO4(-)·2H2O, (I), and with adipic acid, bis(4-carbamoylpiperidinium) adipate dihydrate, 2C6H13N2O(+)·C6H8O4(2-)·2H2O, (II), are three-dimensional hydrogen-bonded constructs involving several different types of enlarged water-bridged cyclic associations. In the structure of (I), the oxalate monoanions give head-to-tail carboxylic acid O-H···O(carboxyl) hydrogen-bonding interactions, forming C(5) chain substructures which extend along a. The isonipecotamide cations also give parallel chain substructures through amide N-H···O hydrogen bonds, the chains being linked across b and down c by alternating water bridges involving both carboxyl and amide O-atom acceptors and amide and piperidinium N-H···O(carboxyl) hydrogen bonds, generating cyclic R4(3)(10) and R3(2)(11) motifs.

2-(4-Amino-benzene-sulfonamido)-4,6-dimethyl-pyrimidin-1-ium 2-carb-oxy-4,6-dinitro-phenolate.

In the structure of the phenolate salt of the sulfa drug sulfamethazine with 3,5-dinitro-salicylic acid, C12H15N4O2S(+)·C7H3N2O7 (-), the dihedral angle between the pyrimidine and benzene rings of the cation is 59.70 (17)°. In the crystal, cation-anion hydrogen-bonding inter-actions involving pyrim-idine-carb-oxy N(+)-H⋯O and amine-carb-oxy N-H⋯O pairs give a cyclic R 2 (2)(8) motif while secondary N-H⋯O hydrogen bonds between the aniline group and both sulfone and nitro O-atom acceptors give a two-dimensional structure extending in (001).

Proton-transfer compounds with 4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide (sulfamethazine): the structures and hydrogen bonding in the salts with 5-nitrosalicylic acid and picric acid.

The structures of the anhydrous proton-transfer compounds of the sulfa drug sulfamethazine with 5-nitrosalicylic acid and picric acid, namely 2-(4-aminobenzenesulfonamido)-4,6-dimethylpyrimidinium 2-hydroxy-5-nitrobenzoate, C12H15N4O2S(+)·C7H4NO4(-), (I), and 2-(4-aminobenzenesulfonamido)-4,6-dimethylpyrimidinium 2,4,6-trinitrophenolate, C12H15N4O2S(+)·C6H2N3O7(-), (II), respectively, have been determined. In the asymmetric unit of (I), there are two independent but conformationally similar cation-anion heterodimer pairs which are formed through duplex intermolecular N(+)-H···O(carboxylate) and N-H···O(carboxylate) hydrogen-bond pairs, giving a cyclic motif [graph set R2(2)(8)]. These heterodimers form separate and different non-associated substructures through aniline N-H···O hydrogen bonds, one one-dimensional, involving carboxylate O-atom acceptors, the other two-dimensional, involving both carboxylate and hydroxy O-atom acceptors.

Hydrogen bonding in two ammonium salts of 5-sulfosalicylic acid: ammonium 3-carboxy-4-hydroxybenzenesulfonate monohydrate and triammonium 3-carboxy-4-hydroxybenzenesulfonate 3-carboxylato-4-hydroxybenzenesulfonate.

The structures of two ammonium salts of 3-carboxy-4-hydroxybenzenesulfonic acid (5-sulfosalicylic acid, 5-SSA) have been determined at 200 K. In the 1:1 hydrated salt, ammonium 3-carboxy-4-hydroxybenzenesulfonate monohydrate, NH4(+)·C7H5O6S(-)·H2O, (I), the 5-SSA(-) monoanions give two types of head-to-tail laterally linked cyclic hydrogen-bonding associations, both with graph-set R4(4)(20). The first involves both carboxylic acid O-H···O(water) and water O-H···O(sulfonate) hydrogen bonds at one end, and ammonium N-H···O(sulfonate) and N-H···O(carboxy) hydrogen bonds at the other.

4-Amino-N-(4,6-dimethyl-pyrimidin-2-yl)benzene-sulfonamide-2-nitro-benzoic acid (1/1).

In the asymmetric unit of the title co-crystal, C(12)H(14)N(4)O(2)S·C(7)H(5)NO(4), the sulfamethazine and 2-nitro-benzoic acid mol-ecules form a heterodimer through inter-molecular amide-carb-oxy-lic acid N-H⋯O and carb-oxy-lic acid-pyrimidine O-H⋯N hydrogen-bond pairs, giving a cyclic motif [graph set R(2) (2)(8)]. The dihedral angle between the two aromatic ring systems in the sulfamethazine mol-ecule is 88.96 (18)° and the nitro group of the acid is 50% rotationally disordered.

4-(4-Nitro-benz-yl)pyridinium 3-carb-oxy-4-hy-droxy-benzene-sulfonate.

In the title salt, C(12)H(11)N(2)O(2) (+)·C(7)H(5)O(6)S(-), the dihedral angle between the benzene and pyridine rings in the 4-(4-nitro-benz-yl)pyridinium cation is 82.7 (2)°. Within the anion there is an intramolecular hydroxy-O-H⋯O(carboxylic acid) bond.

Hydrogen bonding in cyclic imides and amide carboxylic acid derivatives from the facile reaction of cis-cyclohexane-1,2-carboxylic anhydride with o- and p-anisidine and m- and p-aminobenzoic acids.

The structures of the open-chain amide carboxylic acid rac-cis-2-[(2-methoxyphenyl)carbamoyl]cyclohexane-1-carboxylic acid, C(15)H(19)NO(4), (I), and the cyclic imides rac-cis-2-(4-methoxyphenyl)-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione, C(15)H(17)NO(3), (II), chiral cis-3-(1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-yl)benzoic acid, C(15)H(15)NO(4), (III), and rac-cis-4-(1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-yl)benzoic acid monohydrate, C(15)H(15)NO(4)·H(2)O, (IV), are reported. In the amide acid (I), the phenylcarbamoyl group is essentially planar [maximum deviation from the least-squares plane = 0.060 (1) Å for the amide O atom] and the molecules form discrete centrosymmetric dimers through intermolecular cyclic carboxy-carboxy O-H···O hydrogen-bonding interactions [graph-set notation R(2)(2)(8)].

Cyclic imides and an open-chain amide carboxylic acid from the facile reaction of cis-cyclohexane-1,2-carboxylic anhydride with the isomeric monofluoroanilines.

The structures of the cyclic imides cis-2-(2-fluorophenyl)-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione, C(14)H(14)FNO(2), (I), and cis-2-(4-fluorophenyl)-3a,4,5,6,7,7a-hexahydroisoindoline-1,3-dione, C(14)H(14)FNO(2), (III), and the open-chain amide acid rac-cis-2-[(3-fluorophenyl)carbamoyl]cyclohexane-1-carboxylic acid, C(14)H(16)FNO(3), (II), are reported. Cyclic imides (I) and (III) are conformationally similar, with comparable ring rotations about the imide N-C(ar) bond [the dihedral angles between the benzene ring and the five-membered isoindole ring are 55.40 (8)° for (I) and 51.

Bis(benzyl-aminium) 4,5-dichloro-benzene-1,2-dicarboxyl-ate monohydrate.

In the structure of the title salt, 2C(7)H(10)N(+)·C(8)H(2)Cl(2)O(4) (2-)·H(2)O, the two benzyl-aminium anions have different conformations, one being essentially planar and the other having the side chain rotated out of the benzene plane [minimum ring to side-chain C-C-C-N torsion angles = -3.6 (6) and 50.1 (5)°, respectively].

4-Amino-N-(4,6-dimethyl-pyrimidin-2-yl)-benzene-sulfonamide-4-nitro-benzoic acid (1/1).

In the asymmetric unit of the title co-crystal, C(7)H(5)NO(4)·C(12)H(14)N(4)O(2)S, there are two independent but conformationally similar heterodimers, which are formed through inter-molecular N-H⋯O(carb-oxy) and carbox-yl-pyrimidine O-H⋯N hydrogen-bond pairs, giving a cyclic motif [graph set R(2) (2)(8)]. The dihedral angles between the rings in the sulfonamide molecules are 78.77 (8) and 82.

rac-3-exo-Ammonio-7-anti-carb-oxy-tricyclo-[2.2.1.0.(2,6)]heptane-3-endo-carboxyl-ate monohydrate.

The racemic title compound, C(9)H(11)NO(4)·H(2)O, a tricyclic rearranged amino-norbornane dicarb-oxy-lic acid, is a conformationally rigid analogue of glutamic acid and exists as an ammonium-carboxyl-ate zwitterion, with the bridghead carb-oxy-lic acid group anti-related. In the crystal, N-H⋯O and O-H⋯O hydrogen bonds involving the ammonium, carb-oxy-lic acid and water donor groups with both water and carboxyl O-atom acceptors give a three-dimensional framework structure.

4-[(4-Amino-phen-yl)sulfon-yl]aniline-3,5-dinitro-benzoic acid (1/1).

The title compound, C(7)H(4)N(2)O(6)·C(12)H(12)N(2)O(2)S, is a 1:1 cocrystal of the drug dapsone with 3,5-dinitro-benzoic acid. The dihedral angle between the two aromatic rings of the dapsone mol-ecule is 75.4 (2)°, and the dihedral angles between these rings and that of the 3,5-dinitro-benzoic acid are 64.

rac-4-Carbamoylpiperidinium cis-2-car-boxy-cyclo-hexane-1-carboxyl-ate.

In the title racemic salt, C(6)H(13)N(2)O(+)·C(8)H(11)O(4) (-), formed from the reaction of cis-cyclo-hexane-1,2-dicarb-oxy-lic anhydride with isonipecotamide, the cations are linked into duplex chain substructures through both centrosymmetric cyclic head-to-head 'amide motif' hydrogen-bonding associations [graph set R(2) (2)(8)] and 'side-by-side' R(2) (2)(14) associations. The anions are incorporated into the chains through cyclic R(4) (3)(10) inter-actions involving amide and piperidinium N-H⋯O(carbox-yl) hydrogen bonds which, together with inter-anion carb-oxy-lic acid O-H⋯O(carbox-yl) hydrogen bonds, give a two-dimensional layered structure extending along (011).

1,1,3,3-Tetra-ethyl-isoindolin-2-ium chloride.

In the title compound, C(16)H(26)N(+)·Cl(-), the cations and anions form discrete centrosymetric cyclic dimers through N-H⋯Cl hydrogen-bonding associations with graph-set R(4) (2)(8).

4-(4-Amino-phenyl-sulfon-yl)aniline-1,3,5-trinitro-benzene (1/2).

The asymmetric unit of the title co-crystalline 1:2 adduct, C(12)H(12)N(2)O(2)·2C(6)H(3)N(3)O(6), contains two independent mol-ecules of bis-(4-amino-phen-yl) sulfone (the drug Dapsone) and four mol-ecules of 1,3,5-trinitro-benzene and is extended into a two-dimensional hydrogen-bonded network structure through amino N-H⋯O hydrogen-bonding associations with nitro O-atom acceptors. In the two independent Dapsone mol-ecules, the inter-ring dihedral anges are 69.6 (3) and 63.